L-Proline → HCID 53927006, compound

HRID 850595Notes

Reaction equation

HRID 850595 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][N:6]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7][CH2:8][CH2:9][C:10](=O)[CH3:11])[CH3:2].[NH2:21][C:22]1[C:27]([CH:28]=O)=[CH:26][CH:25]=[CH:24][N:23]=1.N1CCC[C@H]1C(O)=O>C(O)C>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][N:6]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:28][C:27]2[C:22](=[N:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1)[CH3:2]

Participants

5

Reactant 3

HCID 145742L-ProlineHCID 7376333-Pyridinecarboxaldehyde, 2-amino-HCID 11119733HCID 11119733, compound

Product 1

HCID 53927006HCID 53927006, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-6 (28 g, 97.4 mmol), 2-amino-3 formylpyridine (15.5 g, 127 mmol), proline (11.2 g, 97.4 mmol) in ethanol (250 mL) was heated at reflux for 15 h. After cooling and evaporation, the residue was chromatographed (silica gel, 1:1 chloroform/ethyl acetate) to give 2-7 as a yellow oil. TLC Rf =0.41 (silica, 70:25:5 chloroform/ethyl acetate/methanol) 1H NMR (300 MHz, CDCl3) δ 9.09 (m, 1H), 8.14 (m, 2H), 7.43 (m, 2H), 4.17 (q, 2H, 7 Hz), 3.9 (2s, 2H), 3.43 (q, 2H, J=7 Hz), 3.07 (m, 2H), 2.18 (m, 2H), 1.42 (s, 9H), 1.25 (m, 3H).

Workup

  1. temperatureat reflux for 15 h
  2. temperatureAfter cooling
  3. customevaporation
  4. customthe residue was chromatographed (silica gel, 1:1 chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-c8e21ce320c44498a5f0733e474907c6
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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